In general, “zeolite” has been used as a generic term for crystalline and porous aluminosilicates, and the basic unit of the structure of the “zeolite” has been (SiO4)4− or (AlO4)5− having a tetrahedral structure. However, it has recently been clarified that a structure peculiar to or analogous to such a “zeolite” is also present in many other oxides such as aluminophosphate.
In addition, the International Zeolite Association (hereinafter, simply referred to as “IZA”) summarizes the definition of the zeolite in W. Meier, D. H. Meier, D. H. Olxon and Ch. Baerlocher, Atlas of Zeolite Structure Types, 4th Edition, Elsevier (1996) (hereinafter, simply referred to as the “Atlas”). According to this Atlas, substances having a similar structure other than aluminosilicate, are described as an object substance in prescribing the structure, and these substances are called as a “zeolite-like material” in the Atlas (With respect to the details of the history concerning this definition, Yoshio Ono and Takeaki Yajima, Zeolite no Kagaku to Kogaku (Science and Engineering of Zeolites), pp. 1–2, published by Kodansha (Jul. 10, 2000) may be referred to).
In the present specification, the definition of “zeolite” follows the above definition as described in Yoshio Ono and Takeaki Yajima, Zeolite no Kagaku to Kogaku (Science and Engineering of Zeolites), pp. 1–2, published by Kodansha (Jul. 10, 2000), where the term “zeolite” may include not only aluminosilicates but also substances (such as titanosilicate) having a structure analogous to the aluminosilicate.
In the present specification, the structures of zeolite and zeolite-like materials are denoted by a structural code using three alphabetic capital letters approved by IZA and originated in the standard substance which has first been used for the clarification of the structure thereof. The structural codes include those contained in Atlas and those approved in the 4th edition, et seq.
In the present specification, the terms “aluminosilicate” and “titanosilicate” are not limited at all by the properties and/or states thereof (such as crystalline or amorphous, or porous or not porous). Therefore, in the present specification, these terms denote “aluminosilicates” and “titanosilicates” of all properties, unless otherwise indicated specifically.
In the present specification, the term “molecular sieve” means an activity or operation for classifying the molecules by the size thereof, and the term also means a substance having such a function. Zeolite is also included in the definition of this molecular sieve (With respect to the details thereon, the portion relating to “molecular sieve” in Hyojun Kagaku Yogo Jiten (Standard Chemical Glossary), edited by the Chemical Society of Japan, published by Maruzen (Mar. 30, 1991) may be referred to).
The “meso-porous body” as used in the present specification is a porous substance having a pore size of 2 to 50 nm (With respect to the details thereon, Yoshio Ono and Tateaki Yajima (compilers), Zeolite no Kagaku to Kogaku (Science and Engineering of Zeolite), pp. 13–23, Kodansha (Jul. 10, 2000) may be referred to).
After the method of synthesizing “TS-1”, which is a zeolite was disclosed in U.S. Pat. No. 4,410,501, various studies have been made on the oxidizing reactions of organic compounds using titanosilicates as the catalyst and peroxides as the oxidizing agent. Specific examples thereof include a method disclosed in JP-A7-242649 (the term “JP-A” as used herein means an “unexamined Japanese patent publication”) where olefin compounds are epoxidized by using a crystalline titanosilicate-containing molecular sieve having a structure similar to zeolite beta having a crystal structure code of *BEA and containing no aluminum, as the catalyst, and using hydrogen peroxide or an organic peroxide as the oxidizing agent.
In the oxidizing reaction of compounds having a carbon-carbon double bond such as an olefin compound, using a titanosilicate catalyst, a ring-opening reaction of the epoxy group is liable to occur on the resultant product of the epoxy compound and, as a result, the selectivity of the epoxy compound is disadvantageously decreased. Further, as the catalytic activity decreasing rate is large in such a reaction, the catalyst must be used in a large amount, or the catalyst must be regenerated very often. Thus, it is difficult in many cases to industrially use the titanosilicate catalyst.
On the other hand, JP-A-10-25285 discloses a method wherein a mixture of alcohol and ketone is co-present in the reaction for epoxidizing an olefin compound with hydrogen peroxide by using a crystalline titanosilicate (TS-1) catalyst having a structure code of ZSM-5.
The addition of the mixture of alcohol and ketone was conducted because, in the oxidizing reaction of an olefin compound using hydrogen peroxide as the oxidizing agent, such an addition had been expected to provide an effect of preventing the production of diol as a by-product due to the ring-opening reaction of the epoxy compound (which proceeds mainly in an aqueous phase). Actually, the above-mentioned patent publication describes an example where the catalytic activity is improved by the addition of the mixture of alcohol and ketone. However, this method has a problem that the solvolysis of an epoxy compound with an alcohol or ketone compound occurs to reduce the selectivity of the epoxide compound and, further, the carbonyl compound such as ketone readily produces an explosive organic peroxide as a by-product.
On the other hand, JP-A-11-171880 discloses a method wherein the reaction system is irradiated with ultrasound and ammonium carbonate is used as the co-catalyst in the epoxidation of an allyl halide with a titanosilicate catalyst and hydrogen peroxide. In the specification of this patent publication, there is described an example wherein when the reaction is performed while being irradiated with ultrasound in the co-presence of ammonium carbonate, the ring-opening reaction of the epoxy compound can be suppressed. However, the ammonium carbonate must be added in a large amount, and the recovery of ammonium carbonate is difficult. Thus, it is problematic to use this method industrially. Further, when ultrasound is irradiated, the catalyst is seriously pulverized into fine powder and it becomes more difficult to separate the catalyst from the reaction mixture and to recover the catalyst.
As described above, although various proposals have been made regarding the oxidizing reaction of an olefin compound using a titanosilicate as the catalyst and a peroxide as the oxidizing agent, the industrially practicable technique is rather limited, and it has not been reported that an intended oxidized compound is obtained with high selectivity by using a simple and easy method in the oxidizing reaction of a carbon-carbon double bond of Compound A.